4242+ Private Villas and Holiday Rentals in Second City |
Second City Holiday Rentals
Apartment
- Chicago
- ·
- Wrigleyville
- 0.23 mi to center
5 Bedrooms
2 Baths
12 Guests
23681 ft²
Fireplace/Heating
Balcony/Terrace
Pet Friendly
Kitchen
US $1,136/Night
7 Nights - US $7,953
Apartment
- Chicago
- ·
- Lake View East
- 0.30 mi to center
10.0Exceptional
(14 Reviews)
1 Bedroom
1 Bath
2 Guests
699.65 ft²
Internet
Child Friendly
US $256/Night
7 Nights - US $1,792
Bed & Breakfast
10.0Exceptional
(517 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
Parking
Air Conditioner
US $339/Night
7 Nights - US $2,375
Apartment
- Chicago
- ·
- Ukrainian Village
- 0.36 mi to center
4 Bedrooms
4 Baths
10 Guests
1600 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,091/Night
7 Nights - US $7,640
Apartment
10.0Exceptional
(8 Reviews)
2 Bedrooms
1 Bath
4 Guests
914.93 ft²
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $618/Night
7 Nights - US $4,329
House
10.0Exceptional
(26 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $531/Night
7 Nights - US $3,717
Apartment
- Chicago
- ·
- Roscoe Village
- 0.31 mi to center
4 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $1,003/Night
7 Nights - US $7,023
Apartment
10.0Exceptional
(4 Reviews)
13 Bedrooms
12 Baths
32 Guests
1435.19 ft²
Private Pool
Hot Tub- Fireplace/Heating
Pool
US $1,582/Night
7 Nights - US $11,076
Bed & Breakfast
9.8Exceptional
(399 Reviews)
1 Bedroom
1 Bath
Spa- Fireplace/Heating
- Balcony/Terrace
Breakfast
US $195/Night
7 Nights - US $1,365
Apartment
- Chicago
- ·
- Rush and Division
- 0.22 mi to center
1 Bedroom
3 Baths
12 Guests
1500 ft²
Oceanfront- Fireplace/Heating
Ocean View
View
US $992/Night
7 Nights - US $6,942
Apartment
- Chicago
- ·
- Lake View East
- 0.18 mi to center
10.0Exceptional
(4 Reviews)
6 Bedrooms
2 Baths
20 Guests
3498.27 ft²
Private Beach- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $645/Night
7 Nights - US $4,515
House
- Chicago
- ·
- East Village
- 0.26 mi to center
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $771/Night
7 Nights - US $5,398
Apartment
10.0Exceptional
(4 Reviews)
3 Bedrooms
1 Bath
2 Guests
355.21 ft²
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $285/Night
7 Nights - US $1,993
New
House
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $767/Night
7 Nights - US $5,367
New
Apartment
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $677/Night
7 Nights - US $4,738
Apartment
- Chicago
- ·
- Wrigleyville
- 0.09 mi to center
2 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $627/Night
7 Nights - US $4,390
Apartment
2 Bedrooms
1 Bath
5 Guests
849 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Internet
US $487/Night
7 Nights - US $3,406
Condo
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $457/Night
7 Nights - US $3,196
Apartment
2 Bedrooms
1 Bath
4 Guests
754 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $442/Night
7 Nights - US $3,093
Apartment
- Chicago
- ·
- Lake View East
- 0.13 mi to center
1 Bedroom
1 Bath
2 Guests
500 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $393/Night
7 Nights - US $2,748
New
Apartment
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $381/Night
7 Nights - US $2,666
Apartment
3 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $172/Night
7 Nights - US $1,201
New
Hotel
- Chicago
- ·
- South Loop
- 0.55 mi to center
2 Baths
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,318/Night
7 Nights - US $9,224
New
Hotel
2 Baths
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,108/Night
7 Nights - US $7,757
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